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cholesterol

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Identification
Molecular formula
C27H46O
CAS number
57-88-5
IUPAC name
(5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
State
State

At room temperature, cholesterol is a solid.

Melting point (Celsius)
148.00
Melting point (Kelvin)
421.20
Boiling point (Celsius)
360.00
Boiling point (Kelvin)
633.20
General information
Molecular weight
386.65g/mol
Molar mass
386.6530g/mol
Density
1.0529g/cm3
Appearence

Cholesterol appears as a white, crystalline powder. It is practically insoluble in water but is soluble in alcohol and other organic solvents, which accounts for its prevalence in fat-rich environments.

Comment on solubility

Solubility

The compound known as (5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol exhibits unique solubility characteristics due to its complex polycyclic structure and multiple functional groups.

Factors Influencing Solubility

  • Polarity: The presence of the hydroxyl (-OH) group significantly affects solubility, as it tends to increase the polarity of the molecule. This can enhance hydrogen bonding with solvents like water.
  • Hydrophobic Regions: The extensive hydrophobic carbon skeleton can lead to limited solubility in polar solvents.
  • Solvent Type: The solubility of this compound in a solvent can vary widely based on whether the solvent is polar (e.g., water, ethanol) or nonpolar (e.g., hexane, toluene).

As a result:

  • It may be soluble in organic solvents, particularly nonpolar ones, due to its hydrocarbon portions.
  • In polar solvents, its solubility may be limited, which is typical for many large organic molecules.

In conclusion, understanding the solubility of this compound is critical for its applications and effectiveness in various chemical contexts. As always, testing the solubility in specific solvents will provide the most accurate information.

Interesting facts

Interesting Facts about (5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol

This compound is a fascinating example in the world of organic chemistry, particularly highlighting the complexity of steroid structures. Here are some intriguing points about this compound:

  • Steroidal Backbone: It possesses a steroid-like structure, which is significant for various biological functions, especially in hormone synthesis.
  • Stereochemistry: The specific stereochemistry, denoted by the multiple S and R configurations, plays a critical role in determining the compound's biological activity and interaction with enzymes or receptors.
  • Natural Occurrence: Compounds with such structures often occur in nature and are related to various plant and animal steroids, contributing to their physiological roles.
  • Potential Uses: Due to its structural properties, this compound could be investigated for potential uses in pharmacology, particularly in developing therapeutic agents.
  • Research Significance: Studying this compound may yield insights into the synthesis pathways of complex steroids, highlighting the importance of chirality in medicinal chemistry.

As quoted by renowned chemists, "The beauty of chemistry lies in the complexity of its structures and the profound implications they hold." This compound embodies that sentiment, showcasing the intricate dance of atoms that can lead to significant biological impacts.

In summary, (5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol is not just a chemical formula; it is a key player in the exploration of biochemical pathways, potential pharmaceuticals, and the riveting world of organic chemistry.

Synonyms
Desoxymethyltestosterone
3275-64-7
Pheraplex
Ba 2665
NSC 63329
Sc 11977
17-Methyl-5-alpha-androst-2-en-17-beta-ol
UNII-B9E9G5A169
NSC-63329
5-alpha-ANDROST-2-EN-17-beta-OL, 17-METHYL-
Androst-2-en-17-ol, 17-methyl-, (5-alpha,17-beta)-
17-alpha-Methyl-(5-alpha)-delta(sup 2)-androstene-17-beta-ol
DTXSID50872931
BA-2665
SC-11977
17.ALPHA.-METHYL-ETIOALLOCHOLAN-2-ENE-17.BETA.-OL
17.BETA.-HYDROXY-17.ALPHA.-METHYL-5.ALPHA.-ANDROST-2-ENE
ANDROST-2-EN-17-OL, 17-METHYL-, (5.ALPHA.,17.BETA.)-
17-methylandrost-2-en-17-ol
17-Methyl-5-.alpha.-androst-2-en-17-.beta.-ol
5-.alpha.-Androst-2-en-17-.beta.-ol, 17-methyl-
Androst-2-en-17-ol, 17-methyl-, (5-.alpha.,17-.beta.)-
17-.alpha.-Methyl-(5-.alpha.)-.delta.(sup 2)-androstene-17-.beta.-ol
Androst-2-en-17-ol, 17-methyl-, (5alpha,17beta)-
DTXCID90820471
17ALPHA-METHYL-ETIOALLOCHOLAN-2-ENE-17BETA-OL
17BETA-HYDROXY-17ALPHA-METHYL-5ALPHA-ANDROST-2-ENE
Madol
Desoxymethyltesterone
(5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
B9E9G5A169
17-alpha-5-alpha-androst-2-en-17beta-ol
Madol (1.0mg/ml in Acetonitrile)
(5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
SCHEMBL929074
CHEBI:79620
NSC63329
DB-214992
17alpha-methyl-5alpha-androst-2-ene-17-ol
NS00068004
Q904694